Monatshefte für Chemie / Chemical Monthly

, Volume 106, Issue 3, pp 679–693 | Cite as

Zum Verhalten von Olefinen, konjugierten Dienen und Steroidolefinen gegenüber Pb(OCOCF3)4

  • Dietmar Westphal
  • Erich Zbiral
Organische Chemie und Biochemie
Received:

Reactions of Pb(OCOCF3)4 with olefines, conjugated dienes and steroid olefines

Abstract

The reaction of Pb(OCOCF3)4 with several olefines and conjugated dienes is reported. The oxidation of styrene, stilbene and 1.4-dihydro-1.4-methanonaphthalene leads to phenylacetaldehyde (1), benzaldehyde (2) and benzophenone (3), and to 1.2.3.4-tetrahydro-1.4-methanonaphthalene-(2S,9R+2R,9S)-diol-bis-trifluoroacetate (8) respectively. Of the conjugated dienes, 1.3-cyclohexadiene yieldscis-2-cyclohexene-1.4-diol bis-trifluoroacetate (4), cyclopentadiene yieldscis-2-cyclopentene-1.4-diolbis-trifluoroacetate (5) andtrans-2-cyclopentene-1.4-diol-bis-trifluoroacetate (6) andE,E-2.4-hexadiene yields the isomers of 3-hexene-2.5-diol bis trifluoroacetate (7). Oxidation of unsaturated steroids such as 2-cholestene, 2-androsten-17-one, 4-cholestene, androsta-4.9(11)-diene-3.17-dione and 3β-acetoxy-5-cholestene results in cholestane-2α,3α-diol diacetate (9), 2α,3α-diacetoxyandrostan-17-one (10) and 1α-acetoxy-2-androsten-17-one (11), in coprostane-4β,5β-diol-4β-trifluoroacetate (12) or coprostane 4β,5β-diol-4β-acetate (12a), 4-cholestanone (13), in 12α-trifluoroacetoxyandrosta-4,9(11)-diene-3.17-dione (14), and in cholestane-3β,5α,6α-triol-3β-acetate-6α-trifluoracetate.

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Copyright information

© Springer-Verlag 1975

Authors and Affiliations

  • Dietmar Westphal
    • 1
  • Erich Zbiral
    • 1
  1. 1.Organisch-Chemischen Institut der Universität WienWienÖsterreich

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